A second generation approach to Actinolide A has been explored utilizing the simple, efficient, and general zinc mediated a-prenylation of aldehydes and ketones developed by Zhao and co-workers. This methodology has been extended to prepare an a-geranylated alcohol, which is a key intermediate in the synthetic approach to Actionlide A. Actinolides A and B are two a,b-unsaturated delta lactones isolated from a methanol extract of the stems of Actinodaphne lancifolia which was shown to have cytotoxic activity against ovarian, lung, breast, pancreatic, lymphoid and leukemia cancers. The presentation below outlines the synthetic approach being used to prepare Actinolide A and its analogues and the improvements from the first generation. Key steps include a Grubb's ring closing metathesis and an a-geranylation of an a,b-unsaturated aldehyde. Upon completion of Actinolide A and its analogues, each analogue will be tested against various cancer cell lines for their cytotoxic activity.

Zinc mediated geranylation: Toward the total synthesis of actinolide A

245th National Meeting (2013)

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